CA1043355A - Halophenoxy benzamide herbicides - Google Patents
Halophenoxy benzamide herbicidesInfo
- Publication number
- CA1043355A CA1043355A CA191,956A CA191956A CA1043355A CA 1043355 A CA1043355 A CA 1043355A CA 191956 A CA191956 A CA 191956A CA 1043355 A CA1043355 A CA 1043355A
- Authority
- CA
- Canada
- Prior art keywords
- compound
- benzamide
- nitro
- plants
- sec
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 239000004009 herbicide Substances 0.000 title abstract description 7
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 title description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 24
- -1 N,N-di(sec-butyl)-2-nitro-5-(2',4'-dichloro-6'--fluorophenoxy)benzamide Chemical compound 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- FIPDPYZWXAOVFG-UHFFFAOYSA-N n-butan-2-yl-5-(2,4-dichloro-6-fluorophenoxy)-2-nitrobenzamide Chemical compound C1=C([N+]([O-])=O)C(C(=O)NC(C)CC)=CC(OC=2C(=CC(Cl)=CC=2F)Cl)=C1 FIPDPYZWXAOVFG-UHFFFAOYSA-N 0.000 claims description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 230000008635 plant growth Effects 0.000 claims 5
- 235000010233 benzoic acid Nutrition 0.000 abstract description 7
- 150000001408 amides Chemical class 0.000 abstract description 2
- 150000001559 benzoic acids Chemical class 0.000 abstract description 2
- 150000002148 esters Chemical class 0.000 abstract description 2
- 150000003839 salts Chemical class 0.000 abstract description 2
- 150000001266 acyl halides Chemical class 0.000 abstract 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 9
- 230000002363 herbicidal effect Effects 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 239000005711 Benzoic acid Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000007921 spray Substances 0.000 description 5
- 238000011282 treatment Methods 0.000 description 5
- 239000007788 liquid Substances 0.000 description 4
- 241000894007 species Species 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- 244000237956 Amaranthus retroflexus Species 0.000 description 3
- 241000196324 Embryophyta Species 0.000 description 3
- 244000299507 Gossypium hirsutum Species 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 240000008042 Zea mays Species 0.000 description 3
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 3
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 235000005822 corn Nutrition 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 235000013479 Amaranthus retroflexus Nutrition 0.000 description 2
- 235000004135 Amaranthus viridis Nutrition 0.000 description 2
- 235000011293 Brassica napus Nutrition 0.000 description 2
- 240000008100 Brassica rapa Species 0.000 description 2
- 235000000540 Brassica rapa subsp rapa Nutrition 0.000 description 2
- 235000009344 Chenopodium album Nutrition 0.000 description 2
- 235000005484 Chenopodium berlandieri Nutrition 0.000 description 2
- 235000009332 Chenopodium rubrum Nutrition 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- 244000152970 Digitaria sanguinalis Species 0.000 description 2
- 235000010823 Digitaria sanguinalis Nutrition 0.000 description 2
- 244000058871 Echinochloa crus-galli Species 0.000 description 2
- 240000002439 Sorghum halepense Species 0.000 description 2
- 238000010752 Ullmann ether synthesis reaction Methods 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 229940076134 benzene Drugs 0.000 description 2
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 235000012343 cottonseed oil Nutrition 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 238000003973 irrigation Methods 0.000 description 2
- 150000004702 methyl esters Chemical class 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 238000005580 one pot reaction Methods 0.000 description 2
- BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 description 2
- 239000002689 soil Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 1
- 150000005435 2-methoxybenzoic acids Chemical class 0.000 description 1
- PKRSYEPBQPFNRB-UHFFFAOYSA-N 2-phenoxybenzoic acid Chemical class OC(=O)C1=CC=CC=C1OC1=CC=CC=C1 PKRSYEPBQPFNRB-UHFFFAOYSA-N 0.000 description 1
- RYAQFHLUEMJOMF-UHFFFAOYSA-N 4-phenoxybenzoic acid Chemical class C1=CC(C(=O)O)=CC=C1OC1=CC=CC=C1 RYAQFHLUEMJOMF-UHFFFAOYSA-N 0.000 description 1
- 241000743987 Alopecurus pratensis Species 0.000 description 1
- 240000001592 Amaranthus caudatus Species 0.000 description 1
- 235000009328 Amaranthus caudatus Nutrition 0.000 description 1
- 235000011331 Brassica Nutrition 0.000 description 1
- 241000220243 Brassica sp. Species 0.000 description 1
- 235000001602 Digitaria X umfolozi Nutrition 0.000 description 1
- 235000017898 Digitaria ciliaris Nutrition 0.000 description 1
- 235000005476 Digitaria cruciata Nutrition 0.000 description 1
- 235000006830 Digitaria didactyla Nutrition 0.000 description 1
- 235000005804 Digitaria eriantha ssp. eriantha Nutrition 0.000 description 1
- 235000014716 Eleusine indica Nutrition 0.000 description 1
- 241000287828 Gallus gallus Species 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- KZPZKNHAIWLBJQ-UHFFFAOYSA-N MC-3761 Chemical compound C1=C([N+]([O-])=O)C(C(=O)OC)=CC(OC=2C(=CC(Cl)=CC=2Cl)Cl)=C1 KZPZKNHAIWLBJQ-UHFFFAOYSA-N 0.000 description 1
- VDTUHFXWUUZATR-UHFFFAOYSA-N MC-7181 Chemical compound C1=C([N+]([O-])=O)C(C(=O)OC)=CC(OC=2C(=CC(Cl)=CC=2F)Cl)=C1 VDTUHFXWUUZATR-UHFFFAOYSA-N 0.000 description 1
- 244000115721 Pennisetum typhoides Species 0.000 description 1
- 235000007195 Pennisetum typhoides Nutrition 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- 241000209504 Poaceae Species 0.000 description 1
- 235000008515 Setaria glauca Nutrition 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 235000012735 amaranth Nutrition 0.000 description 1
- 239000004178 amaranth Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 229940054066 benzamide antipsychotics Drugs 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000002385 cottonseed oil Substances 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 125000005265 dialkylamine group Chemical group 0.000 description 1
- 244000013123 dwarf bean Species 0.000 description 1
- 235000005489 dwarf bean Nutrition 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 229910000286 fullers earth Inorganic materials 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000003450 growing effect Effects 0.000 description 1
- 239000010440 gypsum Substances 0.000 description 1
- 229910052602 gypsum Inorganic materials 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- OBYVIBDTOCAXSN-UHFFFAOYSA-N n-butan-2-ylbutan-2-amine Chemical compound CCC(C)NC(C)CC OBYVIBDTOCAXSN-UHFFFAOYSA-N 0.000 description 1
- 230000000802 nitrating effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000000361 pesticidal effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 238000004382 potting Methods 0.000 description 1
- 230000001902 propagating effect Effects 0.000 description 1
- 229910052903 pyrophyllite Inorganic materials 0.000 description 1
- 230000021217 seedling development Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
- C07C205/57—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C205/59—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton the carbon skeleton being further substituted by singly-bound oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US00334528A US3839444A (en) | 1971-11-01 | 1973-02-22 | Halophenoxy benzamide herbicides |
| US396976A US3873303A (en) | 1971-11-01 | 1973-09-12 | Herbicidal use and compositions of halophenoxy benzamides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1043355A true CA1043355A (en) | 1978-11-28 |
Family
ID=26989254
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA191,956A Expired CA1043355A (en) | 1973-02-22 | 1974-02-07 | Halophenoxy benzamide herbicides |
Country Status (7)
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4173464A (en) * | 1976-05-07 | 1979-11-06 | Sumitomo Chemical Company, Limited | m-Phenoxybenzamide derivatives |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4843609A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1971-10-05 | 1973-06-23 |
-
1974
- 1974-01-25 JP JP1029374A patent/JPS49116230A/ja active Pending
- 1974-02-07 CA CA191,956A patent/CA1043355A/en not_active Expired
- 1974-02-12 GB GB639774A patent/GB1432752A/en not_active Expired
- 1974-02-21 FR FR7405994A patent/FR2218832B2/fr not_active Expired
- 1974-02-21 DE DE19742408433 patent/DE2408433A1/de not_active Ceased
- 1974-02-22 NL NL7402490A patent/NL7402490A/xx not_active Application Discontinuation
- 1974-04-08 IT IT2087874A patent/IT1049529B/it active
-
1978
- 1978-07-28 JP JP9162578A patent/JPS5444023A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| DE2408433A1 (de) | 1974-09-19 |
| IT1049529B (it) | 1981-02-10 |
| GB1432752A (en) | 1976-04-22 |
| FR2218832B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1977-06-10 |
| NL7402490A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1974-08-26 |
| JPS49116230A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1974-11-06 |
| JPS5444023A (en) | 1979-04-07 |
| FR2218832A2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1974-09-20 |
| JPS5510563B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1980-03-17 |
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